2-Amino-1-(3-chloro-phenyl)-5-phenyl-1H-pyrrole-3-carbonitrile | 122238-03-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-Amino-1-(3-chloro-phenyl)-5-phenyl-1H-pyrrole-3-carbonitrile
• 英文别名: 2-Amino-1-(3-chlorophenyl)-5-phenylpyrrole-3-carbonitrile
• CAS: 122238-03-3
• 化学式: C₁₇H₁₂ClN₃
• 分子量: 293.755
• InChiKey: NNQKOZQONLKYIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.7
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Amino-1-(3-chloro-phenyl)-5-phenyl-1H-pyrrole-3-carbonitrile 、 邻苯二胺 在 盐酸 作用下， 以 水 为溶剂， 反应 6.0h， 以66%的产率得到3-(1H-benzimidazol-2-yl)-1-(3-chlorophenyl)-5-phenyl-pyrrol-2-amine
  参考文献：
  名称：

  Synthesis and docking studies of novel antitumor benzimidazoles

  摘要：

  In this work, the benzimidazole-pyrrole conjugates 6a-h and benzimidazole-tetracycles conjugates 12-14 were prepared. The cytotoxicity of the compounds 3, 4a-h, 6a-h, 8, 10 and 12-14 was tested against lung cancer cell line A549. Compound 6b exhibited higher activity than the bis-benzoxazole natural product (UK-1), the standard. The tested 4g, h, 6a-h, 10 and 12-14 exhibited remarkable cytotoxicity activity against breast cancer cell line MCF-7 with higher activity than tamoxifen. Furthermore, compound 4h was found to be also more potent than doxurubicin. The antitumor promotion activity of synthesized compounds 4g, h, 6a-h, 10 and 12-14 has been estimated by studying their possible inhibitory effects on EBV-EA activation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA). Among the studied compounds, the inhibitory activities of compounds 8, 13 and 14 demonstrated strong inhibitory effects on the Epstein-Barr virus early antigen (EBV-EA) activation without showing any cytotoxicity on the Raji cells and their effects being stronger than that of a representative control, oleanolic acid.Moreover, the molecular docking of the new compounds into plasminogen activator (uPA) receptor has been in correlation with the antitumor activity. All synthesized compounds 3, 4a-h, 6a-h, 8, 10 and 12-14 were docked into same groove of the binding site of the native co-crystalized (4-iodobenzo[b]thiophene-2-carboxamidine) ligand (PDB code: 1c5x) for activity explaination. Compounds 4h, 6b and 13, giving the best docking results, were further studied to estimate their effect on the level of uPA using AssayMax human urokinase (uPA) ELISA kit. In case of A549 cell line, compound 6 exhibited similar activity to MMC, and for MCF-7 cell line, compound 4h exhibited similar activity to doxorubicin, in inhibiting the expression of uPA. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.10.010
• 作为产物：
  描述：

  (2-氧代-2-苯基乙基)丙二腈 、 3-氯苯胺 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 120.0h， 以45%的产率得到2-Amino-1-(3-chloro-phenyl)-5-phenyl-1H-pyrrole-3-carbonitrile
  参考文献：
  名称：

  Hilmy, Khalid Mohamed Hassan; Pedersen, Erik B., Liebigs Annalen der Chemie, 1989, p. 1145 - 1146

  摘要：

  DOI：

文献信息

• Hilmy, Khalid Mohamed Hassan; Pedersen, Erik B., Liebigs Annalen der Chemie, 1989, p. 1145 - 1146
  作者：Hilmy, Khalid Mohamed Hassan、Pedersen, Erik B.

  DOI：——

  日期：——
• HILMY, KHALID MOHAMED HASSAN;PEDERSEN, ERIK B., LIEBIGS ANN. CHEM.,(1989) N1, C. 1145-1146
  作者：HILMY, KHALID MOHAMED HASSAN、PEDERSEN, ERIK B.

  DOI：——

  日期：——
• Synthesis and docking studies of novel antitumor benzimidazoles
  作者：Mohamed A. Omar、Yasser M. Shaker、Shadia A. Galal、Mamdouh M. Ali、Sean M. Kerwin、Jing Li、Harukuni Tokuda、Raghda A. Ramadan、Hoda I. El Diwani

  DOI：10.1016/j.bmc.2012.10.010

  日期：2012.12

  In this work, the benzimidazole-pyrrole conjugates 6a-h and benzimidazole-tetracycles conjugates 12-14 were prepared. The cytotoxicity of the compounds 3, 4a-h, 6a-h, 8, 10 and 12-14 was tested against lung cancer cell line A549. Compound 6b exhibited higher activity than the bis-benzoxazole natural product (UK-1), the standard. The tested 4g, h, 6a-h, 10 and 12-14 exhibited remarkable cytotoxicity activity against breast cancer cell line MCF-7 with higher activity than tamoxifen. Furthermore, compound 4h was found to be also more potent than doxurubicin. The antitumor promotion activity of synthesized compounds 4g, h, 6a-h, 10 and 12-14 has been estimated by studying their possible inhibitory effects on EBV-EA activation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA). Among the studied compounds, the inhibitory activities of compounds 8, 13 and 14 demonstrated strong inhibitory effects on the Epstein-Barr virus early antigen (EBV-EA) activation without showing any cytotoxicity on the Raji cells and their effects being stronger than that of a representative control, oleanolic acid.Moreover, the molecular docking of the new compounds into plasminogen activator (uPA) receptor has been in correlation with the antitumor activity. All synthesized compounds 3, 4a-h, 6a-h, 8, 10 and 12-14 were docked into same groove of the binding site of the native co-crystalized (4-iodobenzo[b]thiophene-2-carboxamidine) ligand (PDB code: 1c5x) for activity explaination. Compounds 4h, 6b and 13, giving the best docking results, were further studied to estimate their effect on the level of uPA using AssayMax human urokinase (uPA) ELISA kit. In case of A549 cell line, compound 6 exhibited similar activity to MMC, and for MCF-7 cell line, compound 4h exhibited similar activity to doxorubicin, in inhibiting the expression of uPA. (C) 2012 Elsevier Ltd. All rights reserved.